Síntese de compostos com potencial atividade biológica: 1,2,3-triazóis-1,4-dissubstituídos derivados do AZT e de 1,3-benzocalcogenazóis-2-arilsubstituídos

Abstract

In this present work, an unprecedented series of 1,2,3-triazoles derived from AZT 9 was synthesized from benzocalcogenazol 7 and AZT, this union is of great interest due to the biological activities that these nucleus possess. The compounds 7a-b were obtained through an SN2 reaction in 50% and 60% yields. To synthesize the 1,2,3-triazoles derived from AZT 9a-b was carried out from a Click type reaction in the presence of the CuI catalyst, where the yield obtained for both products was 96%. With the products 9 synthesized, the hydroxyl (OH) of zidovudine was protected in two different ways, these being: mesylation using mesylate chloride to obtain the ((2S,3R,5R)-3-(4-(((4-(benzo[d]thiazol-2-yl)phenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl) methyl methanesulfonate 10, and through acetylation using acetic anhydride to obtain the ((2S,3R,5R)-3-(4-(((4-(benzo[d]thiazol-2-yl)phenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl) methyl acetate 12. All the structures obtained were characterized by analysis of the spectra of 1H and 13C.